N-benzylquinoline-3-carboxamide | 5382-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-benzylquinoline-3-carboxamide
• 英文别名: N-(Phenylmethyl)-3-quinolinecarboxamide
• CAS: 5382-46-7
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: PUPUJBMVSMVBLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴喹啉 在 potassium fluoride 、 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-benzylquinoline-3-carboxamide
  参考文献：
  名称：

  Palladium-Catalyzed Fluorocarbonylation Using N-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives

  摘要：

  N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.

  DOI：

  10.1021/ol4026815

文献信息

• N-Phenyl-4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R phosphoinositide-3-kinase (PI3Kα)
  作者：Dima A. Sabbah、Neka A. Simms、Wang Wang、Yuxiang Dong、Edward L. Ezell、Michael G. Brattain、Jonathan L. Vennerstrom、Haizhen A. Zhong

  DOI：10.1016/j.bmc.2012.09.059

  日期：2012.12

  efforts to optimize the lead PI3Kα inhibitor N-benzyl 4-hydroxy-2-quinolone-3-carboxamide using structure-based design and molecular docking. We identified a series of N-phenyl 4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R versus wild-type PI3Kα and we also showed that the cell growth inhibition by these compounds likely occurs by inhibiting the formation of pAKT and induction

  这项工作描述了我们使用基于结构的设计和分子对接来优化先导 PI3Kα 抑制剂N-苄基 4-羟基-2-喹诺酮-3-甲酰胺的努力。我们鉴定了一系列N-苯基 4-羟基-2-喹诺酮-3-甲酰胺作为突变体 H1047R 与野生型 PI3Kα 的选择性抑制剂，我们还表明这些化合物可能通过抑制 pAKT 的形成来抑制细胞生长和诱导细胞凋亡。
• Cobalt nanoparticle-catalysed <i>N</i>-alkylation of amides with alcohols
  作者：Rui Ma、Jie Gao、Lan Zhang、Ning Wang、Yue Hu、Stephan Bartling、Henrik Lund、Sebastian Wohlrab、Rajenahally V. Jagadeesh、Matthias Beller

  DOI：10.1039/d3gc03286h

  日期：——

  A protocol for efficient N-alkylation of benzamides with alcohols in the presence of cobalt-nanocatalysts is described. Key to the success of this general methodology is the use of highly dispersed cobalt nanoparticles supported on carbon, which are obtained from the pyrolysis of cobalt(II) acetate and o-phenylenediamine as a ligand at suitable temperatures. The catalytic material shows a broad substrate

  描述了在钴纳米催化剂存在下苯甲酰胺与醇的有效N-烷基化的方案。这种通用方法成功的关键是使用碳负载的高度分散的钴纳米颗粒，这些纳米颗粒是通过乙酸钴( II )和邻苯二胺作为配体在合适的温度下热解而获得的。该催化材料表现出广泛的底物范围和对官能团良好的耐受性。除了合成各种仲酰胺（> 45 种产品）外，该催化剂还可以转化更具挑战性的脂肪醇和酰胺，包括生物基酰胺和大分子酰胺。成功的回收和再利用强调了催化剂的实际适用性。
• Expedient carbonylation of aryl halides in aqueous or neat condition
  作者：Wei Jie Ang、Lee-Chiang Lo、Yulin Lam

  DOI：10.1016/j.tet.2014.09.065

  日期：2014.11

  An expedient and versatile, microwave-assisted procedure for the carbonylation of aryl halides with boronic acids, alcohols or amines in water or under neat conditions has been developed. The reaction is catalyzed by fluorous, oxime-based palladacycle 1 that shows an excellent recyclable property and low levels of Pd leaching. To demonstrate the usefulness of the protocol, we applied it to the preparation of compounds of pharmaceutical interest, including a precursor of the reverse transcriptase inhibitor, niacin, benzocaine and butamben. (C) 2014 Elsevier Ltd. All rights reserved.
• Iron Pentacarbonyl in Alkoxy- and Aminocarbonylation of Aromatic Halides
  作者：Matej Babjak、Oľga Caletková、Diana Ďurišová、Tibor Gracza

  DOI：10.1055/s-0034-1379227

  日期：——

  We have identified reaction conditions for a Heck-type carbonylation based on [Fe(CO)(5)]. Preliminary optimization of alkoxycarbonylation on 2-bromonaphthalene defined functioning composition of the reaction mixture which was then applied on a small set of (hetero)aromatic halides. Respective aminocarbonylation of these halides with different amines, including aniline and benzotriazole, was accomplished with reasonable results.
• Amides of Nicotinic Acid and Related Acids. II
  作者：John H. Billman、John L. Rendall

  DOI：10.1021/ja01232a011

  日期：1944.4